2,3-디클로로-5,6-디시아노-1,4-벤조퀴논
2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 · DDQ · 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE · 2,3-dicyano-5,6-dichloro-p-benzoquinone · 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile · 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE · 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE · Dichlorodicyanobenzoquinone
식별자 및 물리적 특성
| CAS No. | 84-58-2 |
|---|---|
| 분자식 | C8Cl2N2O2 |
| 평균 분자량 | 227 g/mol |
| 단동위원소 질량 | 225.9336826 g/mol |
| SMILES | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O |
| InChIKey | HZNVUJQVZSTENZ-UHFFFAOYSA-N |
| PubChem CID | 6775 |
| ChEMBL | CHEMBL3759231 |
| EC No. | 201-542-2 |
| DTXSID | DTXSID7052577 |
| 현지명 | 2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 |
화학 및 물리적 성질
| XLogP | 1.6 |
|---|---|
| 극성 표면적 | 81.7 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 464 |
| 물질 분류 | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| Physical Description | Yellow to orange solid[Merck Index] Dark yellow powder[Alfa Aesar MSDS] |
| 녹는점 | 210-215 °C (dec.)(lit.) |
| 끓는 점 | 301.8±42.0 °C(Predicted) |
| 밀도 | 1.7500 (estimate) |
| 저장 조건 | Store below +30°C. |
| 용해도 | 벤젠, 메탄올, 아세트산 및 디옥산에 용해됩니다. 클로로포름, 디클로로메탄에 약간 용해됩니다. |
| 물리적 상태 | 결정질 분말 또는 결정 |
| 색상 | 노란색에서 주황색으로 |
| 용해도 | 물과 반응 |
| Merck | 14,3063 |
| BRN | 747939 |
| InChI | 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13 |
| InChIKey | HZNVUJQVZSTENZ-UHFFFAOYSA-N |
| SMILES | ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O |
| NIST | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2) |
| EPA | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2) |
화학적 성질
yellow to orange powder
안전 및 규제
| GHS 분류 | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 77 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-Status: Active Update: 01-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/213372,3-Dichloro-5,6-dicyano-p-benzoquinone: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | Intraperitoneal LD50 (mouse) = 31 mg/kgIntravenous LD50 (mouse) = 13 mg/kg[RTECS] Decomposed by water[Merck Index] Reacts with water evolving toxic gasesAn irritantToxic by ingestion[Alfa Aesar MSDS] See Hydroquinone. See NITRILES. |
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | GU4825000 |
| 운송 번호(UN) | UN 3439 6.1/PG 3 |
| 관세 코드 | 29269095 |
| 위험 문구(R) | 25-29-41-37/38-20/21-23/24/25 |
| 위험 표시 | T |
| 안전 문구(S) | 22-24/25-37-45-36/37-26-36/37/39 |
| 포장분류 | II |
| 위험 등급 | 6.1Acute Tox. 3 Oral |
| F 고인화성물질 | 21 |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
용도
개요
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has a variety of applications. DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of quinolones and an oxidizing agent used to synthesize steroids. Additionally, DDQ is used with Ph3P to synthesize 1,2-benzisoxazoles.
용도
An oxidizing agent, especially in steroid synthesis.2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.
제조 및 합성 방법
제조 방법
The first synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was described by J.Thiele and F.Guntber in 1906. However, no interest was shown in the compound until Linstead and co-workers discovered its extraordinary potency as a dehydrogenating agent. Its oxidation potential is greater than that of any other known quinone.2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation